JP2015520232A5 - - Google Patents
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- Publication number
- JP2015520232A5 JP2015520232A5 JP2015518471A JP2015518471A JP2015520232A5 JP 2015520232 A5 JP2015520232 A5 JP 2015520232A5 JP 2015518471 A JP2015518471 A JP 2015518471A JP 2015518471 A JP2015518471 A JP 2015518471A JP 2015520232 A5 JP2015520232 A5 JP 2015520232A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triazine
- carboxamide
- aminocyclohexyl
- oxobutan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 84
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- -1 2-aminocyclohexyl Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 7
- HNUXGKGGWIBQRA-JGVFFNPUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(1,3-thiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2SC=NC=2)=N1 HNUXGKGGWIBQRA-JGVFFNPUSA-N 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 210000004027 cell Anatomy 0.000 claims description 5
- DEFDSCVFDCEKRD-CQSZACIVSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 DEFDSCVFDCEKRD-CQSZACIVSA-N 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 102000000551 Syk Kinase Human genes 0.000 claims description 4
- 108010016672 Syk Kinase Proteins 0.000 claims description 4
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- DXFZQDKXRIAXCS-UHFFFAOYSA-N triazine-4-carboxamide Chemical compound NC(=O)C1=CC=NN=N1 DXFZQDKXRIAXCS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002062 proliferating effect Effects 0.000 claims description 3
- PQKKCWZAVROFQE-CQSZACIVSA-N 3-[[(1R)-2-amino-2-oxo-1-phenylethyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@@H](C(N)=O)C=2C=CC=CC=2)=NN=C1C(N)=O PQKKCWZAVROFQE-CQSZACIVSA-N 0.000 claims description 2
- CJSRBVUNMJDWMX-ZWNOBZJWSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(1,3-benzothiazol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3SC=NC3=CC=2)=N1 CJSRBVUNMJDWMX-ZWNOBZJWSA-N 0.000 claims description 2
- BDPFQPDNLKMIRN-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dihydro-1H-isochromen-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3CCOCC3=CC=2)=N1 BDPFQPDNLKMIRN-UKRRQHHQSA-N 0.000 claims description 2
- OSCMRAHNENPVLT-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dihydro-1H-isochromen-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3COCCC3=CC=2)=N1 OSCMRAHNENPVLT-UKRRQHHQSA-N 0.000 claims description 2
- MIUDQKHEQLFZDL-ZYHUDNBSSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=CC=2)=N1 MIUDQKHEQLFZDL-ZYHUDNBSSA-N 0.000 claims description 2
- VCJFEQDOPCFCLU-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-cyano-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C#N)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O VCJFEQDOPCFCLU-TZMCWYRMSA-N 0.000 claims description 2
- NBMOCOIZELAEOS-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-fluoro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O NBMOCOIZELAEOS-DGCLKSJQSA-N 0.000 claims description 2
- RKXKXSVTGYIPFR-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-fluoro-5-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC(F)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 RKXKXSVTGYIPFR-DGCLKSJQSA-N 0.000 claims description 2
- NOMBWPRYIHPSJP-BXUZGUMPSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-methoxy-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 NOMBWPRYIHPSJP-BXUZGUMPSA-N 0.000 claims description 2
- KKBWWFNLCNYCPL-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 KKBWWFNLCNYCPL-DGCLKSJQSA-N 0.000 claims description 2
- VOKZNAYAXGUXNN-ZWNOBZJWSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-chloro-3-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 VOKZNAYAXGUXNN-ZWNOBZJWSA-N 0.000 claims description 2
- REYYDCRADMMODN-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O REYYDCRADMMODN-DGCLKSJQSA-N 0.000 claims description 2
- HPBIFDFZFXESSX-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 HPBIFDFZFXESSX-UKRRQHHQSA-N 0.000 claims description 2
- VCKQCHJOYBTTEN-BXKDBHETSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(thieno[2,3-b]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3SC=2)=N1 VCKQCHJOYBTTEN-BXKDBHETSA-N 0.000 claims description 2
- QHDISYZLXHMZSG-BXUZGUMPSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N QHDISYZLXHMZSG-BXUZGUMPSA-N 0.000 claims description 2
- SSRKQGJJCKUAOW-IUODEOHRSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N SSRKQGJJCKUAOW-IUODEOHRSA-N 0.000 claims description 2
- VRJOHUABISCHSG-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylpyrrolo[2,3-b]pyridin-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1N=C2N(C)C=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N VRJOHUABISCHSG-DGCLKSJQSA-N 0.000 claims description 2
- JKXVQLLPGGEPAF-IUODEOHRSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-oxidoquinolin-1-ium-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=[N+]([O-])C3=CC=2)=N1 JKXVQLLPGGEPAF-IUODEOHRSA-N 0.000 claims description 2
- YGPZKVFXMSUASF-CZUORRHYSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N YGPZKVFXMSUASF-CZUORRHYSA-N 0.000 claims description 2
- JLXTZYUHNQKVCP-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[3-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=N1 JLXTZYUHNQKVCP-TZMCWYRMSA-N 0.000 claims description 2
- VZLDOVQMBPXEET-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[4-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C=2OC=CN=2)=N1 VZLDOVQMBPXEET-TZMCWYRMSA-N 0.000 claims description 2
- LOWCUSYAFWXQOY-VHSXEESVSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=3SC=NC=3C=CC=2)=N1 LOWCUSYAFWXQOY-VHSXEESVSA-N 0.000 claims description 2
- ACPFBGHGHDRKKQ-WCQYABFASA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(2-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C(=CC=CC=2)C#N)=N1 ACPFBGHGHDRKKQ-WCQYABFASA-N 0.000 claims description 2
- GZMMACCMYHRVBG-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-chloro-5-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=C(F)C=2)=N1 GZMMACCMYHRVBG-NWDGAFQWSA-N 0.000 claims description 2
- UZGHIRRQDQJKMH-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C#N)=N1 UZGHIRRQDQJKMH-QWHCGFSZSA-N 0.000 claims description 2
- IMHGLGQUEBDRKS-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-fluoro-5-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC(F)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 IMHGLGQUEBDRKS-QWHCGFSZSA-N 0.000 claims description 2
- LCHIDYRCIZWTGU-LSDHHAIUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-pyrazol-1-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=C2)=N1 LCHIDYRCIZWTGU-LSDHHAIUSA-N 0.000 claims description 2
- ZDYDGWOIXLZZOV-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 ZDYDGWOIXLZZOV-NWDGAFQWSA-N 0.000 claims description 2
- CMQIMQMMVHHQED-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-cyano-3-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(C#N)=CC=2)=N1 CMQIMQMMVHHQED-QWHCGFSZSA-N 0.000 claims description 2
- PHRQFJRAMFZEQK-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C#N)=N1 PHRQFJRAMFZEQK-QWHCGFSZSA-N 0.000 claims description 2
- FEQOCZZXMBAWLC-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-fluoro-3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(C)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 FEQOCZZXMBAWLC-QWHCGFSZSA-N 0.000 claims description 2
- REURUSXMYWMZJD-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(F)=CC=2)=N1 REURUSXMYWMZJD-NWDGAFQWSA-N 0.000 claims description 2
- XBCHLHAAWPFOHD-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O XBCHLHAAWPFOHD-QWHCGFSZSA-N 0.000 claims description 2
- OIWFJDIUCRBTGQ-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(imidazo[1,2-a]pyridin-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=CC3=NC=CN3C=C2)=N1 OIWFJDIUCRBTGQ-NWDGAFQWSA-N 0.000 claims description 2
- AFEVUZLPGUTJEX-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(pyrazolo[1,5-a]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=C3C=CC=CN3N=C2)=N1 AFEVUZLPGUTJEX-WDEREUQCSA-N 0.000 claims description 2
- YHKAHEUHVDHAHC-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(1-methylindazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N YHKAHEUHVDHAHC-QWHCGFSZSA-N 0.000 claims description 2
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- QZHWAWCKFNNRET-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(2-methoxypyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NC(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 QZHWAWCKFNNRET-WDEREUQCSA-N 0.000 claims description 2
- JELUIACODZYMFB-LSDHHAIUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N JELUIACODZYMFB-LSDHHAIUSA-N 0.000 claims description 2
- VWVLRQSCZNBNIE-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(3-phenyl-1,2,4-oxadiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2ON=C(N=2)C=2C=CC=CC=2)=N1 VWVLRQSCZNBNIE-NWDGAFQWSA-N 0.000 claims description 2
- UBSXBZOWHDCART-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(5-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=NC=2)=N1 UBSXBZOWHDCART-WDEREUQCSA-N 0.000 claims description 2
- QXLFUYGITUBBPW-VHSXEESVSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(6-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=NC(F)=CC=2)=N1 QXLFUYGITUBBPW-VHSXEESVSA-N 0.000 claims description 2
- SBIJHNZIRKOTDP-DZGCQCFKSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(6-fluoroquinolin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=C(F)C=CC3=NC=2)=N1 SBIJHNZIRKOTDP-DZGCQCFKSA-N 0.000 claims description 2
- CGPCLXAGIFELSI-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=N1 CGPCLXAGIFELSI-UONOGXRCSA-N 0.000 claims description 2
- WPCQGAGVKSOZNX-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 WPCQGAGVKSOZNX-NWDGAFQWSA-N 0.000 claims description 2
- RQRDEGAALIJFDE-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(N3C(COCC3)=O)=CC=2)=N1 RQRDEGAALIJFDE-UONOGXRCSA-N 0.000 claims description 2
- RLRPPGGWMWHWIE-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1,2,4-triazol-1-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)N2N=CN=C2)=N1 RLRPPGGWMWHWIE-UONOGXRCSA-N 0.000 claims description 2
- GYKTYEVNORPXBF-ZAGLGSKWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1-methyl-1-oxidopiperidin-1-ium-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1C[N+](C)([O-])CCC1C(C=C1)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O GYKTYEVNORPXBF-ZAGLGSKWSA-N 0.000 claims description 2
- OQJJAWMFUMTGEQ-RBUKOAKNSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1-propanoylpiperidin-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CN(C(=O)CC)CCC1C(C=C1)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O OQJJAWMFUMTGEQ-RBUKOAKNSA-N 0.000 claims description 2
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- CQLPUHUAFIQJHP-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(dimethylcarbamoyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O CQLPUHUAFIQJHP-UONOGXRCSA-N 0.000 claims description 2
- OMWSSROGEUAMKM-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)N2N=CC=N2)=N1 OMWSSROGEUAMKM-UONOGXRCSA-N 0.000 claims description 2
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- ZXZJQXVGLXVUIB-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 ZXZJQXVGLXVUIB-ZYHUDNBSSA-N 0.000 claims description 2
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- KVMWGQOHPRNIJP-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 KVMWGQOHPRNIJP-ZYHUDNBSSA-N 0.000 claims description 2
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- YRRJXVQAIUEAOB-MERJSTESSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,2,3,4-tetrahydronaphthalen-2-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2CC3=CC=CC=C3CC2)=N1 YRRJXVQAIUEAOB-MERJSTESSA-N 0.000 claims description 2
- DIXOLQVHMWYDKN-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CSC3=CC=2)=N1 DIXOLQVHMWYDKN-WDEREUQCSA-N 0.000 claims description 2
- DXJDHIQZTRGKBX-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3SC=NC3=CC=2)=N1 DXJDHIQZTRGKBX-WDEREUQCSA-N 0.000 claims description 2
- DZAPLSLRQLBYMB-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,5-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=NC=2)=N1 DZAPLSLRQLBYMB-NWDGAFQWSA-N 0.000 claims description 2
- KCOICATWZFXLGO-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,8-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=NC=2)=N1 KCOICATWZFXLGO-QWHCGFSZSA-N 0.000 claims description 2
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- DUFXKLJOXRIASW-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3,4-difluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(F)=CC=2)=N1 DUFXKLJOXRIASW-NWDGAFQWSA-N 0.000 claims description 2
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- CWMZXHYLOWBPQH-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3,5-difluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=C(F)C=2)=N1 CWMZXHYLOWBPQH-NWDGAFQWSA-N 0.000 claims description 2
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- JXOWSEQICYZREV-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(imidazo[1,2-a]pyridin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=CN3C=CN=C3C=C2)=N1 JXOWSEQICYZREV-NWDGAFQWSA-N 0.000 claims description 2
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- VBQXOKGMXNJYLC-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(thieno[2,3-b]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3SC=2)=N1 VBQXOKGMXNJYLC-WDEREUQCSA-N 0.000 claims description 2
- HGJHRMSEHCXAOV-WCQYABFASA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N HGJHRMSEHCXAOV-WCQYABFASA-N 0.000 claims description 2
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- MMRQTMXTTUQLPS-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N MMRQTMXTTUQLPS-UONOGXRCSA-N 0.000 claims description 2
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- BOGZHIUPUYYAMC-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[4-methoxy-3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C(OC)=CC=2)C(F)(F)F)=N1 BOGZHIUPUYYAMC-SECBINFHSA-N 0.000 claims description 2
- HTQLFIUQDWMMDB-OAHLLOKOSA-N 3-[[(2r)-1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC=2C=C(F)C=CC=2)C(N)=O)=NN=C1C(N)=O HTQLFIUQDWMMDB-OAHLLOKOSA-N 0.000 claims description 2
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| EP (1) | EP2863748B1 (https=) |
| JP (1) | JP6281984B2 (https=) |
| CN (1) | CN104470363A (https=) |
| AU (1) | AU2013277476B2 (https=) |
| CA (1) | CA2876945C (https=) |
| IL (1) | IL236057B (https=) |
| IN (1) | IN2014KN02906A (https=) |
| SG (2) | SG10201805392YA (https=) |
| WO (1) | WO2013192049A2 (https=) |
| ZA (1) | ZA201409256B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013047813A1 (ja) * | 2011-09-30 | 2013-04-04 | 大鵬薬品工業株式会社 | １，２，４－トリアジン－６－カルボキサミド誘導体 |
| HK1211024A1 (en) | 2012-10-19 | 2016-05-13 | 霍夫曼-拉罗奇有限公司 | Inhibitors of syk |
| MY194668A (en) | 2012-11-08 | 2022-12-12 | Bristol Myers Squibb Co | Amide-substituted heterocyclic compounds useful as modulators of il-12, il-23 and/or ifn() responses |
| RU2655604C2 (ru) * | 2013-01-11 | 2018-05-29 | Фуджифилм Корпорэйшн | Азотсодержащее гетероциклическое соединение или его соль |
| WO2014111031A1 (zh) * | 2013-01-17 | 2014-07-24 | 四川恒康发展有限责任公司 | 三嗪化合物、其药用盐、异构体或水合物及其药物组合物 |
| JP2016113366A (ja) * | 2013-03-29 | 2016-06-23 | 大鵬薬品工業株式会社 | アセトアミド基を有する１，２，４−トリアジン−６−カルボキサミド誘導体 |
| AU2014360446A1 (en) * | 2013-12-05 | 2016-06-09 | Pharmacyclics, Llc | Inhibitors of Bruton's tyrosine kinase |
| BR112017025986A2 (pt) * | 2015-06-02 | 2018-08-14 | Pharmacyclics Llc | inibidores de tirosina quinase de bruton. |
| CN109384774B (zh) * | 2017-08-11 | 2023-02-17 | 中国科学院上海药物研究所 | 一类多取代的吡嗪/三嗪酰胺类化合物及其制备方法和应用 |
| US12428395B2 (en) | 2019-08-01 | 2025-09-30 | Sperogenix Therapeutics Limited | Heterocyclic compounds as kinase inhibitor and uses thereof |
| CN115003667B (zh) * | 2020-02-26 | 2025-04-15 | 百济神州有限公司 | Tyk-2抑制剂 |
| WO2022032484A1 (zh) * | 2020-08-11 | 2022-02-17 | 北京诺诚健华医药科技有限公司 | 哒嗪-3-甲酰胺类化合物、其制备方法及其在医药学上的应用 |
| WO2023108536A1 (en) * | 2021-12-16 | 2023-06-22 | Lynk Pharmaceuticals Co. Ltd. | Tyk2 inhibitors and compositions and methods thereof |
| EP4448514A4 (en) * | 2021-12-16 | 2025-10-29 | Lynk Pharmaceuticals Co Ltd | TYK2 INHIBITORS AND ASSOCIATED COMPOSITIONS AND PROCESSES |
| WO2024254832A1 (en) * | 2023-06-15 | 2024-12-19 | Lynk Pharmaceuticals Co. Ltd. | Tyk2 inhibitors and compositions and methods thereof |
| CN118175828B (zh) * | 2024-05-16 | 2024-08-16 | 浙江大华技术股份有限公司 | 吸波材料、制备方法和器件 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5107900A (en) * | 1999-06-09 | 2000-12-28 | Yamanouchi Pharmaceutical Co., Ltd. | Novel heterocyclic carboxamide derivatives |
| JP4622047B2 (ja) * | 1999-06-09 | 2011-02-02 | アステラス製薬株式会社 | 新規なヘテロ環カルボキサミド誘導体 |
| WO2000076980A1 (en) * | 1999-06-10 | 2000-12-21 | Yamanouchi Pharmaceutical Co., Ltd. | Novel nitrogen-contaiing heterocyclic derivatives or salts thereof |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| SG2014015085A (en) | 2008-04-16 | 2014-06-27 | Portola Pharm Inc | 2,6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinases inhibitors |
| WO2013047813A1 (ja) * | 2011-09-30 | 2013-04-04 | 大鵬薬品工業株式会社 | １，２，４－トリアジン－６－カルボキサミド誘導体 |
| UY34807A (es) * | 2012-05-16 | 2013-12-31 | Novartis Ag | Derivados monocíclicos de heteroarilcicloalquil- diamina |
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2013
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- 2013-06-14 CA CA2876945A patent/CA2876945C/en active Active
- 2013-06-14 CN CN201380037312.3A patent/CN104470363A/zh active Pending
- 2013-06-14 EP EP13807456.2A patent/EP2863748B1/en active Active
- 2013-06-14 SG SG10201805392YA patent/SG10201805392YA/en unknown
- 2013-06-14 SG SG11201408232RA patent/SG11201408232RA/en unknown
- 2013-06-14 JP JP2015518471A patent/JP6281984B2/ja active Active
- 2013-06-14 WO PCT/US2013/046006 patent/WO2013192049A2/en not_active Ceased
- 2013-06-14 IN IN2906KON2014 patent/IN2014KN02906A/en unknown
- 2013-06-14 AU AU2013277476A patent/AU2013277476B2/en not_active Ceased
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2014
- 2014-12-04 IL IL236057A patent/IL236057B/en active IP Right Grant
- 2014-12-15 ZA ZA2014/09256A patent/ZA201409256B/en unknown
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